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Note | Regular issue | Vol 71, No. 8, 2007, pp.1843-1849
Published online, 25th May, 2007
DOI: 10.3987/COM-07-11084
Synthesis of Enantiomerically Pure (+)- and (-)-3-Methyl-3-(2-naphthyl)-2H-
benzo[e][1,2]thiazine 1,1,4-Triones

Zhao-Peng Liu*

*Department of Organic Chemistry, School of Pharmaceutical Sciences, Shandong University, No. 44, WenHua XiLu, Jinan 250012, China


Treatment of N-t-butylbenzenesulfonamide with an excess of BuLi, followed by the reaction with methyl 2-naphthylpropanoate, gave the corresponding 2-carboxybenzenesulfonamide, which underwent cyclization under TMSCl-NaI-MeCN reflux conditions to afford the N-sulfonylimine. Bromination of the N-sulfonylimine and ring expansion mediated by 20% KOH (aq.), formed the 3-methyl-3-(2-naphthyl)benzo[e][1,2]thiazine 1,1,4-trione. Optical resolution of the racemic benzosultam using (-)-menthoxyacetyl chloride, furnished the (+)- and (-)- 3-methyl-3-(2-naphthyl)benzo[e][1,2]thiazine 1,1,4-triones.